Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

Abstract

We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

Keywords

nickel catalysis - vinylation - cross-coupling - Hiyama coupling - ligand-free conditions - vinylsilane - aryl halide

Publication History

Received: 30 November 2020

Accepted after revision: 31 January 2021

Accepted Manuscript online:
31 January 2021

Article published online:
16 February 2021

• References and Notes

• 1a Grubbs RH. Tetrahedron 2004; 60: 7117
• 1b Ogba OM, Warner NC, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
• 2 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
• 3a Chen J, Lu Z. Org. Chem. Front. 2018; 5: 260
• 3b Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
• 3c Fan WW, Li L, Zhang GQ. J. Org. Chem. 2019; 84: 5987
• 3d Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48
• 3e Agbossou F, Carpentier JF, Mortreux M. Chem. Rev. 1995; 95: 2485
• 4 Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX. Chem. Rev. 2005; 105: 1603
• 5a Hirao A, Goseki R, Ishizone T. Macromolecules 2014; 47: 1883
• 5b Goseki R, Tanaka S, Ishizone T, Hirao A. React. Funct. Polym. 2018; 127: 94
• 6 Emerson WS. Chem. Rev. 1949; 45: 347
• 7a Maryanoff B, Reitz A. Chem. Rev. 1989; 89: 863
• 7b Bisceglia JA, Orelli LR. Curr. Org. Chem. 2012; 16: 2206
• 8 Chinchilla R, Najera C. Chem. Rev. 2014; 114: 1783
• 9 Denmark S, Butler CR. Chem. Commun. 2009; 20
• 10 Bumagin NA, Luzikova EV. J. Organomet. Chem. 1997; 532: 271
• 11 Hornillos V, Giannerini M, Vila C, Fañanás-Mastrala M, Feringa BL. Chem. Sci. 2015; 6: 1394
• 12 Schumann H, Kaufmann J, Schmalz H.-G, Bottcher A, Gotov B. Synlett 2003; 1783
• 13a Kerins F, O’Shea DF. J. Org. Chem. 2002; 67: 4968
• 13b Kesslers A, Coleman CM, Charoenying P, O’Shea DF. J. Org. Chem. 2004; 69: 7836
• 13c Molander GA, Rivero MR. Org. Lett. 2002; 4: 107
• 13d Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
• 13e Alacid E, Najera C. J. Org. Chem. 2009; 74: 8191
• 13f Civicos JF, Alonso DA, Najera C. Adv. Synth. Catal. 2011; 353: 1683
• 14a Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
• 14b Itami K, Nokami T, Yoshidaj J. J. Am. Chem. Soc. 2001; 123: 5600
• 14c Hosoi K, Nozaki K, Hiyama T. Chem. Lett. 2002; 2: 138
• 14d Nakao Y, Imanaka H, Sahoo AK, Yada A, Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
• 14e Denmark SE, Sweis RF, Wehrli D. J. Am. Chem. Soc. 2004; 126: 4865
• 14f Denmark SE, Butler CR. J. Am. Chem. Soc. 2008; 130: 3690
• 14g Gordillo AL, Jesus ED, Carmen LM. J. Am. Chem. Soc. 2009; 131: 4584
• 14h Premi C, Jain N. Eur. J. Org. Chem. 2013; 5493
• 14i Yang C.-T, Han J, Liu J, Li Y, Zhang F, Yu H.-Z, Hu S, Wang X. Chem. Eur. J. 2018; 24: 10324
• 14j Faßbender SI, Molloy JJ, Mück-Lichtenfeld C, Gilmour R. Angew. Chem. Int. Ed. 2019; 58: 18619
• 15a William J, Scott WJ, Stille JK. J. Am. Chem. Soc. 1986; 108: 3033
• 15b Grasa GA, Nolan SP. Org. Lett. 2001; 3: 119
• 15c Littke AF, Schwarz L, Fu GC. J. Am. Chem. Soc. 2002; 124: 6343

For selected reviews on Ni-catalyzed coupling reactions, see:
• 16a Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
• 16b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
• 16c Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
• 16d Su B, Cao ZC, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
• 16e Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
• 16f Weix DJ. Acc. Chem. Res. 2015; 48: 1767
• 16g Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
• 16h Henrion M, Ritleng V, Chetcuti MJ. ACS Catal. 2015; 5: 1283
• 16i Choi J, Fu GC. Science 2017; 356: eaaf7230
• 16j Modern Organonickel Chemistry. Tamaru Y. Wiley-VCH; Weinheim: 2006
• 17 Kiso Y, Yamamoto K, Tamao K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
• 18 Yamamoto T, Yamakawa T. J. Org. Chem. 2009; 74: 3603
• 19 Liu J, Ren Q, Zhang X, Gong H. Angew. Chem. Int. Ed. 2016; 55: 15544

For reviews, see:
• 20a Monfared A, Mohammadi B, Ahmadi S, Nikpassan M, Hosseinian A. RSC Adv. 2019; 9: 3185
• 20b Organosilicon Chemistry. Hiyama T, Oestreich M. Wiley-VCH; Weinheim: 2019
• 20c Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631

For selected examples on coupling reaction of aryl silicon compounds and alkyl halides, see:
• 21a Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
• 21b Powell DA, Fu GC. J. Am. Chem. Soc. 2004; 126: 7788
• 21c Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
• 21d Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc. 2008; 130: 3302

For selected examples on coupling reaction of aryl silicon compounds and aryl halides, see:
• 22a Tang S, Takeda M, Nakao Y, Hiyamaz T. Chem. Commun. 2011; 47: 307
• 22b Tang S, Li SH, Nakao Y, Hiyamaz T. Asian J. Org. Chem. 2013; 2: 416
• 23a Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5628
• 23b Cai Y, Zhang J.-W, Li F, Liu J.-M, Shi S.-L. ACS Catal. 2019; 9: 1
• 23c Cai Y, Ye X, Liu S, Shi S.-L. Angew. Chem. Int. Ed. 2019; 58: 13433
• 23d Shen D, Zhang W.-B, Li Z, Shi S.-L, Xu Y. Adv. Synth. Catal. 2020; 362: 1125
• 23e Li Y.-Q, Li F, Shi S.-L. Chin. J. Chem. 2020; 38: 1035
• 23f Cai Y, Ruan L.-X, Rahman A, Shi S.-L. Angew. Chem. Int. Ed. 2021; 60: in press
• 23g Li Y.-Q, Shi S.-L. Chin. J. Org. Chem. 2021; 41: in press,
• 24 For a similar Pd-catalyzed C–O bond-forming reaction using vinyltrimethoxysilane and electron-deficient aryl halides, see: Milton EJ, Fuentes JA, Clarke ML. Org. Biomol. Chem. 2009; 7: 2645
• 25a Pilcher AS, Ammon HL, DeShong P. J. Am. Chem. Soc. 1995; 117: 5166
• 25b Pilcher AS, DeShong P. J. Org. Chem. 1996; 61: 6901
• 26a Brescia M.-R, DeShong P. J. Org. Chem. 1998; 63: 3156
• 26b Mowery ME, DeShong P. J. Org. Chem. 1999; 64: 3266
• 27 General Procedure 1 In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), 18-crown-6 (121.0 mg, 0.46 mmol, 2.3 equiv), KOMe (32.2 mg, 0.46 mmol, 2.3 equiv), NiCl₂(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMF (1.0 mL) were charged to an 8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (68.0 mg, 0.46 mmol, 2.3 equiv) was added. The vial was removed from the glove box, and the reaction mixture was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc and washed with water. The organic phase was dried over Na₂SO₄, filtered, and concentrated, and the residue was purified by column chromatography on silica gel to give the product. 2-Methoxy-6-vinylnaphthalene (3a) Using general procedure 1: white solid, 31.0 mg, yield: 84%. ¹H NMR (400 MHz, CDCl₃): δ = 7.78–7.66 (m, 3 H), 7.62 (dd, J = 8.7, 1.7 Hz, 1 H), 7.19–7.10 (m, 2 H), 6.87 (dd, J = 17.6, 10.9 Hz, 1 H), 5.84 (dd, J = 17.6, 0.9 Hz, 1 H), 5.30 (dd, J = 10.9, 0.9 Hz, 1 H), 3.93 (s, 3 H). General Procedure 2 In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0 equiv), TBAT (270 mg, 0.5 mmol, 2.5 equiv), NiCl₂(glyme) (4.4 mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an 8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane (59.1 mg, 0.4 mmol, 2.0 equiv) was added. The vial was removed from the glove box, and the reaction mixture was stirred at rt (35 °C) for 12 h. The reaction mixture was then diluted with EtOAc and washed with water. The organic phase was dried over Na₂SO₄, filtered, and concentrated, and the residue was purified by column chromatography on silica gel to give the product. 2-Vinylnaphthalene (3b) Using general procedure 2: white solid, 25.5 mg, yield: 83%. ¹H NMR (400 MHz, CDCl₃): δ = 7.85–7.79 (m, 3 H), 7.76 (s, 1 H), 7.65 (dd, J = 8.6, 1.7 Hz, 1 H), 7.50–7.42 (m, 2 H), 6.90 (dd, J = 17.6, 10.9 Hz, 1 H), 5.89 (dd, J = 17.6, 0.8 Hz, 1 H), 5.35 (dd, J = 10.9, 0.8 Hz, 1 H).